Unique Phenanthrenes from
Juncaceae
Juncus ensifolius
antiproliferative
combination assay
doxorubicin
phenanthrene
synergism
Journal
Pharmaceutics
ISSN: 1999-4923
Titre abrégé: Pharmaceutics
Pays: Switzerland
ID NLM: 101534003
Informations de publication
Date de publication:
10 Mar 2022
10 Mar 2022
Historique:
received:
11
02
2022
revised:
07
03
2022
accepted:
08
03
2022
entrez:
26
3
2022
pubmed:
27
3
2022
medline:
27
3
2022
Statut:
epublish
Résumé
Phenanthrenes are the main special metabolites of Juncaceae species from phytochemical, pharmacological, and chemotaxonomical points of view. The present study focused on the isolation, structure determination, and pharmacological investigation of phenanthrenes from Juncus ensifolius. Nineteen compounds, including 17 phenanthrenes, were identified from the methanol extract of the plant. Thirteen compounds, namely, ensifolins A−M (1−13), were obtained for the first time from natural sources. Four phenanthrenes [2-hydroxy-1,7-dimethyl-5-vinyl-9,10-dihydrophenanthrene (14), juncuenin B (15), juncatrin B (16), and sylvaticin A (17)], 4-hydroxybenzaldehyde (18) and luteolin (19) were isolated for the first time from J. ensifolius. Ensifolins A (1) and B (2) are structurally unique phenanthrenes, considering that they are flavonoid- (1) or benzaldehyde-adducts (2). The antiproliferative activity of all isolated compounds against HeLa, COLO 205, and COLO 320 cancer cells and a non-tumor (MRC-5) cell line was tested using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) viability assay. The luteolin-substituted phenanthrene ensifolin A (1) proved to be the most active against all three cancer cell lines (IC50 values 3.9−12.7 μM) and showed good selectivity (SI = 4.95) in the case of COLO 205. The best selectivity was recorded for ensifolins D (4, SI > 5.15, HeLa), H (8, SI > 8.13, HeLa), and 17 (SI > 9.43, HeLa). The synergistic activity of the compounds with doxorubicin was also tested on HeLa cells, and ensifolins E (5) and H (8) exhibited very strong synergism (CI < 0.1). In conclusion, these phenanthrenes are worthy of further investigation.
Identifiants
pubmed: 35335985
pii: pharmaceutics14030608
doi: 10.3390/pharmaceutics14030608
pmc: PMC8949129
pii:
doi:
Types de publication
Journal Article
Langues
eng
Subventions
Organisme : Ministry of Human Capacities
ID : GINOP-2.3.2-15-2016-00012
Organisme : Ministry of Human Capacities
ID : UNKP-20-3-II
Organisme : Ministry of Human Capacities
ID : EFOP-3.6.3-VEKOP-16-2017-00009
Organisme : National Research, Development and Innovation Office
ID : K128963
Références
Molecules. 2018 Aug 20;23(8):
pubmed: 30127296
Diseases. 2015 Oct 22;3(4):260-281
pubmed: 28943624
J Nat Prod. 2020 Mar 27;83(3):770-803
pubmed: 32162523
J Agric Food Chem. 2015 Sep 9;63(35):7700-6
pubmed: 25625345
Biotechnol Adv. 2020 Jan - Feb;38:107382
pubmed: 30978386
J Nat Prod. 2018 Mar 23;81(3):661-678
pubmed: 29280630
J Nat Prod. 2020 Nov 25;83(11):3250-3261
pubmed: 33064469
J Chem Ecol. 1996 Mar;22(3):587-603
pubmed: 24227494
Dalton Trans. 2019 Jul 16;48(28):10464-10478
pubmed: 31125040
Biochem Pharmacol. 2016 Mar 15;104:8-18
pubmed: 26774454
Front Oncol. 2022 Feb 02;11:789172
pubmed: 35211395
Int J Mol Sci. 2021 Oct 06;22(19):
pubmed: 34639131
Anticancer Res. 2012 Apr;32(4):1379-86
pubmed: 22493374
J Nat Prod. 2009 Jun;72(6):1209-12
pubmed: 19514742
Biomed Pharmacother. 2021 Feb;134:111102
pubmed: 33338743
Phytomedicine. 2019 May;58:152770
pubmed: 31005716
Molecules. 2020 May 20;25(10):
pubmed: 32443866
Biomed Pharmacother. 2019 Aug;116:108852
pubmed: 30999152
Cancer Res. 2010 Jan 15;70(2):440-6
pubmed: 20068163
Toxicol Appl Pharmacol. 2015 Sep 1;287(2):98-110
pubmed: 25982451
Pharmacol Rev. 2006 Sep;58(3):621-81
pubmed: 16968952
Fitoterapia. 2017 Jan;116:131-138
pubmed: 27940118
Appl Environ Microbiol. 1996 Sep;62(9):3355-9
pubmed: 8795226